Abstract
The amine 8-{4-[(6-phenyl-pyridin-3-yl)meth-yl]piperazin-1-yl}-3,4-di-hydro-quinolin-2(1H)-one was crystallized as the hydro-chloride salt, 4-(2-oxo-1,2,3,4-tetra-hydro-quinolin-8-yl)-1-[(6-phenyl-pyridin-3-yl)meth-yl]piperazin-1-ium chloride, C25H27N4 +·Cl- (I·HCl). The conformation of the organic cation is half-moon in shape enclosing the chloride anion. The piperidine ring of the 3,4-di-hydro-quinolin-2(1H)-one moiety has a screw-boat conformation, while the piperazine ring has a chair conformation. In the biaryl group, the pyridine ring is inclined to the phenyl ring by 40.17 (7) and by 36.86 (8)° to the aromatic ring of the quinoline moiety. In the crystal, the cations are linked by pairwise N-H⋯O hydrogen bonds, forming inversion dimers enclosing an R 2 2(8) ring motif. The Cl- anion is linked to the cation by an N-H⋯Cl hydrogen bond. These units are linked by a series of C-H⋯O, C-H⋯N and C-H⋯Cl hydrogen bonds, forming layers lying parallel to the ab plane.
Highlights
The amine 8-{4-[(6-phenylpyridin-3-yl)methyl]piperazin-1-yl}-3,4-dihydroquinolin-2(1H)-one was crystallized as the hydrochloride salt, 4-(2-oxo-1,2,3,4tetrahydroquinolin-8-yl)-1-[(6-phenylpyridin-3-yl)methyl]piperazin-1-ium chloride, C25H27N4+ÁClÀ (IÁHCl)
The ClÀ anion is linked to the cation by an N—HÁ Á ÁCl hydrogen bond
These units are linked by a series of C—HÁ Á ÁO, C—HÁ Á ÁN and C—HÁ Á ÁCl hydrogen bonds, forming layers lying parallel to the ab plane
Summary
Schizophrenia is a psychiatric illness afflicting over 1% of the world’s population. Adoprazine# and Bifeprunox# (Fig. 1) are two drugs that were developed for the treatment of Schizophrenia in the early 2000s. In continuing efforts in this field, Ullah and collaborators have synthesized a series of compounds that are structural analogues of Adoprazine# and Bifeprunox# (Ullah, 2012, 2014a,b; Ullah & Al-Shaheri, 2012) These include a number of 1-aryl-4-(biarylmethylene)piperazines (Ullah, 2012), such as 8-{4-[(6-phenylpyridin3-yl)methyl]piperazin-1-yl}-3,4-dihydroquinolin-2(1H)-one (I), and 8-(4-{[6-(4-fluorophenyl)pyridin-3-yl]methyl}piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one (II) Ghani et al (2014) have reported that the D2 receptor binding affinity of compounds I and II are Ki = 28.4 nM for I and 42.0 nM for II. The two cations differ essentially in the conformation of the biaryl group (rings B = N4/C15–C19 and C = C20–C25) and their orientation with respect to the aromatic ring (A = C4–C9) of the 3,4-dihydroquinolin-2(1H)one moiety The piperazine ring (N2/N3/C10–C13) has a chair conformation
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